US3969406A - Process for the production of carnitine - Google Patents
Process for the production of carnitine Download PDFInfo
- Publication number
- US3969406A US3969406A US05/572,316 US57231675A US3969406A US 3969406 A US3969406 A US 3969406A US 57231675 A US57231675 A US 57231675A US 3969406 A US3969406 A US 3969406A
- Authority
- US
- United States
- Prior art keywords
- trimethylammonium
- conducted
- sub
- halide
- carnitine hydrochloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 229960004203 carnitine Drugs 0.000 title description 4
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 title 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- JXXCENBLGFBQJM-FYZOBXCZSA-N [(2r)-3-carboxy-2-hydroxypropyl]-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)C[C@H](O)CC(O)=O JXXCENBLGFBQJM-FYZOBXCZSA-N 0.000 claims abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000000375 suspending agent Substances 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- CJLSDBRIXZFCKV-UHFFFAOYSA-N 4-chloro-3-oxo-n-phenylbutanamide Chemical class ClCC(=O)CC(=O)NC1=CC=CC=C1 CJLSDBRIXZFCKV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 4
- -1 β-hydroxy-α-bromobutyric acid ester Chemical class 0.000 description 4
- YXQKBMVBURNTMC-UHFFFAOYSA-N 4-chloro-n-methyl-3-oxo-n-phenylbutanamide Chemical compound ClCC(=O)CC(=O)N(C)C1=CC=CC=C1 YXQKBMVBURNTMC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YTYSUPNFVFLVND-UHFFFAOYSA-N CC(CC(NC1=CC=CC=C1)=O)=O.Cl Chemical compound CC(CC(NC1=CC=CC=C1)=O)=O.Cl YTYSUPNFVFLVND-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RJTROOIXLNVHNB-UHFFFAOYSA-N 4-bromo-3-oxo-n-phenylbutanamide Chemical class BrCC(=O)CC(=O)NC1=CC=CC=C1 RJTROOIXLNVHNB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005703 Trimethylamine hydrochloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- ZCXOSDRICFIHTA-UHFFFAOYSA-N n-methylaniline;hydrochloride Chemical compound [Cl-].C[NH2+]C1=CC=CC=C1 ZCXOSDRICFIHTA-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
Definitions
- This invention relates to a process for the production of carnitine hydrochloride.
- epichlorohydrin is first of all reacted with trimethylaminehydrochloride, the reaction product is converted with NaCN into the carnitine nitrile chloride and the latter is hydrolyzed to carnitine (see U.S. Pat. No. 3,135,788). In such process the products of all the intermediate steps are isolated. The yield amounts to about 74 percent.
- This invention includes a process for the production of carnitine hydrochloride.
- the process includes reacting a ⁇ -haloacetoacetanilide having the formula:
- X is a halogen atom and Y is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, with trimethylamine, a ⁇ -trimethylammonium acetoacetanilide halide resulting.
- the ⁇ -trimethylammonium acetoacetanilide halide is hydrogenated, a ⁇ -trimethylammonium- ⁇ -hydroxybutyric acid halide resulting.
- the ⁇ -trimethylammonium- ⁇ -hydroxybutyric acid halide is converted by means of aqueous hydrochloric acid into carnitine hydrochloride.
- the first reaction step and the hydrogenation step are conducted in the presence of an organic solvent or suspension agent or of water.
- the first reaction step is conducted at a temperature between 20° and 70°C.
- the hydrogenation step is conducted catalytically, and preferably the catalyst is platinum and/or activated charcoal.
- the hydrogenation step is conducted at a H 2 -pressure between 5 and 70 atmospheres.
- the hydrogenation step is conducted at a temperature between 0° and 50°C.
- ⁇ -haloacetoacetanilides are the ⁇ -bromoacetoacetanilides and the ⁇ -chloroacetoacetanilides (preferred).
- ⁇ -haloacetoacetanilides includes derivatives, such as, ⁇ -haloacetoacetalkylanilides, ⁇ -haloacetoacetbenzylanilides, ⁇ -haloacetoacetphenylanilides.
- Useful ⁇ -haloacetoacetalkylanilides are those having 1 to 8 carbon atoms in the alkyl group-examples thereof are ⁇ -bromoacetoacet-N-ethylanilide, ⁇ -bromoacetoacet-N-methylanilide, ⁇ -bromoacetoacet-N-octylanilide, ⁇ -bromoacetoacet-N-isopropylanilide, ⁇ -bromoacetoacet-N-butylanilide, ⁇ -bromoacetoacet-N-pentylanilide, ⁇ -chloroacetoacet-N-methylanilide, ⁇ -chloroacetoacet-N-ethylanilide, ⁇ -chloroacetoacet-N-pentylanilide, ⁇ -chloroacetoace-N-octylanilide, ⁇ -chloroacetoacet-N-heptylanilide
- Examples of useful ⁇ -haloacetoacetphenylanilides are ⁇ -chloroacetoacetphenylanilide and ⁇ -bromoacetoacetphenylanilide.
- Examples of useful ⁇ -haloacetoacetbenzylanilides are ⁇ -chloroacetoacetbenzylanilide and ⁇ -bromoacetoacetbenzylanilide.
- the most preferred ⁇ -haloacetoacetanilide is ⁇ -chloroacetoacetanilide.
- the reaction of the ⁇ -haloacetoacetanilide with trimethylamine and the hydrogenation of the ⁇ -trimethylammonium acetoacetanilide chloride are conducted in water or in an organic solvent or suspension agent.
- organic solvents or suspension agents are methanol, ethanol, isopropanol, propanol, butanol, acetonitrile, dimethyl sulfoxide and dimethyl formamide.
- the reaction of trimethylamine with the ⁇ -haloacetoacetanilide is preferably done at a temperature between 20° and 70°C.
- the hydrogenation is preferably carried out catalytically and most preferably using hydrogen and using platinum or activated charcoal as the catalyst.
- the hydrogenation step is preferably conducted at a temperature from 0° to 50°C and a H 2 pressure of 5 to 70 atm.
- the process of this invention is distinguished by the fact, that it is a so called “one course” process, that is to say the products of the individual steps do not need to be isolated.
- the yields which can be achieved according to the process of this invention lie at about 75 to 85 percent, or more.
- this invention involves reacting ⁇ -chlorocetoacetic acid anilide with trimethylamine to give a ⁇ -trimethylammonium acetoacetic acid anilide chloride, which is hydrogenated to a ⁇ -trimethylammonium- ⁇ -hydroxybutyric acid anilide chloride, which in turn is converted by means of aqueous hydrochloric acid into carnitine hydrochloride.
- the catalyst was filtered off. The filtrate was evaporated, 30 ml of water and 20 ml of concentrated hydrochloric acid were added and the mixture was heated during 3 hours to 100°C. The mixture was filtered and was evaporated until dry on a rota-vaporator at 80°C. After that, the mixture was reacted with 75 ml of isopropanol and 75 ml of ethanol, and then filtered. After standing for 1 hour in a refrigerator at 3° to 5°C, the crystals were filtered off. The crystals were washed with isopropanol and were dried in high vacuum.
- carnitine hydrochloride was obtained by precipitation with ethanol-isopropanol.
- the carnitine hydrochloride had a melting point of 196.5° to 197°C. and the yield amounted to 77.5 percent.
- the filtrate was concentrated, was reacted with 35 ml of concentrated hydrochloric acid and was hydrolyzed during 3 hours at boiling temperature.
- the solution was filtered and was evaporated until dry in a rota-vaporator.
- the solid residue was suspended in 110 ml of ethanol at 0° to 5°C, whereby the N-methylaniline hydrochloride was dissolved and it was possible to filter off the carnitine hydrochloride.
- the crystalline product had a melting point of 197° to 198.5°C and was identical to an authentic sample.
- the yield was 82 percent, based on the ⁇ -chloroacetoacetic acid-N-methylanilide.
- the solid residue was suspended in 60 ml of ethanol at 0° to 5°C., whereby the anilinehydrochloride was dissolved and the carnitinehydrochloride could be filtered off.
- the product had a melting point of 198° to 199°C and was identical to an authentic sample. The yield amounted to 84 percent, based on the ⁇ -chloroacetoacetic anilide.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Respiratory Apparatuses And Protective Means (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5730/74 | 1974-04-26 | ||
| CH573074A CH589604A5 (ru) | 1974-04-26 | 1974-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3969406A true US3969406A (en) | 1976-07-13 |
Family
ID=4298393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/572,316 Expired - Lifetime US3969406A (en) | 1974-04-26 | 1975-04-28 | Process for the production of carnitine |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3969406A (ru) |
| JP (1) | JPS50148312A (ru) |
| AR (1) | AR207361A1 (ru) |
| AT (1) | AT342792B (ru) |
| BE (1) | BE828456A (ru) |
| BG (1) | BG26371A3 (ru) |
| BR (1) | BR7502510A (ru) |
| CA (1) | CA1034143A (ru) |
| CH (1) | CH589604A5 (ru) |
| DD (1) | DD119575A5 (ru) |
| DE (1) | DE2518813C2 (ru) |
| DK (1) | DK174575A (ru) |
| ES (1) | ES436902A1 (ru) |
| FR (1) | FR2268787B1 (ru) |
| GB (1) | GB1448081A (ru) |
| IE (1) | IE41115B1 (ru) |
| IN (1) | IN144611B (ru) |
| IT (1) | IT1035450B (ru) |
| LU (1) | LU72363A1 (ru) |
| NL (1) | NL7504852A (ru) |
| NO (1) | NO751472L (ru) |
| RO (1) | RO66137A (ru) |
| SE (1) | SE404691B (ru) |
| SU (1) | SU544366A3 (ru) |
| ZA (1) | ZA752563B (ru) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3344085A1 (de) * | 1982-12-06 | 1984-06-07 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A., Rom/Roma | Verfahren zur herstellung von l-carnitin und zwischenprodukte fuer das verfahren |
| US4788322A (en) * | 1987-07-31 | 1988-11-29 | Merck & Co., Inc. | Process for preparing ACHPA |
| US4895979A (en) * | 1988-02-19 | 1990-01-23 | Takasago International Corporation | Process for preparing carnitine |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4642290A (en) * | 1982-12-06 | 1987-02-10 | Sih Charles J | Process for preparing a compound for use in the production of L-carnitine |
| US4710468A (en) * | 1983-10-24 | 1987-12-01 | Sigma-Tau Industrie Pharmaceutiche Riunite S.P.A. | Process for preparing L-carnitine and chemical intermediates employed therein |
| IT1190358B (it) * | 1985-05-24 | 1988-02-16 | Sclavo Spa | Procedimento per la preparazione di l-carnitina |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2328021A (en) * | 1940-07-17 | 1943-08-31 | Emuisol Corp | Derivatives of amines |
| US2530627A (en) * | 1946-09-06 | 1950-11-21 | Merck & Co Inc | Production of n-acyl allothreonine esters |
| US2571755A (en) * | 1948-12-09 | 1951-10-16 | Merck & Co Inc | Preparation of threonine and intermediates therefor |
| US3038007A (en) * | 1958-05-23 | 1962-06-05 | Reeve Edward Wilkins | Process for the preparation of dl-threonine |
| US3096368A (en) * | 1958-07-30 | 1963-07-02 | Process for preparing hydrolysis products of gamma-dimethyl amin-beta-hydroxybutyroni | |
| US3135788A (en) * | 1959-09-28 | 1964-06-02 | Nihon Zoki Seiyaku Kabushikika | Preparation of dl-carnitine hydrochloride from trimethylamine hydrochloride and epihalogenohydrin |
| US3462485A (en) * | 1965-03-12 | 1969-08-19 | Belge Produits Chimiques Sa | Process for the preparation of l- and d-carnitine chlorides |
-
1974
- 1974-04-26 CH CH573074A patent/CH589604A5/xx not_active IP Right Cessation
-
1975
- 1975-01-01 AR AR258495A patent/AR207361A1/es active
- 1975-04-16 GB GB1561275A patent/GB1448081A/en not_active Expired
- 1975-04-21 ZA ZA00752563A patent/ZA752563B/xx unknown
- 1975-04-21 IE IE892/75A patent/IE41115B1/xx unknown
- 1975-04-23 DK DK174575A patent/DK174575A/da not_active Application Discontinuation
- 1975-04-24 BR BR3188/75D patent/BR7502510A/pt unknown
- 1975-04-24 JP JP50051258A patent/JPS50148312A/ja active Pending
- 1975-04-24 IT IT49276/75A patent/IT1035450B/it active
- 1975-04-24 NL NL7504852A patent/NL7504852A/xx not_active Application Discontinuation
- 1975-04-24 NO NO751472A patent/NO751472L/no unknown
- 1975-04-24 SE SE7504782A patent/SE404691B/xx unknown
- 1975-04-24 BG BG029774A patent/BG26371A3/xx unknown
- 1975-04-24 ES ES436902A patent/ES436902A1/es not_active Expired
- 1975-04-25 BE BE155838A patent/BE828456A/xx unknown
- 1975-04-25 LU LU72363A patent/LU72363A1/xx unknown
- 1975-04-25 AT AT320575A patent/AT342792B/de not_active IP Right Cessation
- 1975-04-25 RO RO7582091A patent/RO66137A/ro unknown
- 1975-04-25 DD DD185713A patent/DD119575A5/xx unknown
- 1975-04-25 SU SU2127884A patent/SU544366A3/ru active
- 1975-04-25 FR FR7513098A patent/FR2268787B1/fr not_active Expired
- 1975-04-28 US US05/572,316 patent/US3969406A/en not_active Expired - Lifetime
- 1975-04-28 DE DE2518813A patent/DE2518813C2/de not_active Expired
- 1975-04-28 CA CA225,629A patent/CA1034143A/en not_active Expired
- 1975-06-13 IN IN1172/CAL/75A patent/IN144611B/en unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2328021A (en) * | 1940-07-17 | 1943-08-31 | Emuisol Corp | Derivatives of amines |
| US2530627A (en) * | 1946-09-06 | 1950-11-21 | Merck & Co Inc | Production of n-acyl allothreonine esters |
| US2571755A (en) * | 1948-12-09 | 1951-10-16 | Merck & Co Inc | Preparation of threonine and intermediates therefor |
| US3038007A (en) * | 1958-05-23 | 1962-06-05 | Reeve Edward Wilkins | Process for the preparation of dl-threonine |
| US3096368A (en) * | 1958-07-30 | 1963-07-02 | Process for preparing hydrolysis products of gamma-dimethyl amin-beta-hydroxybutyroni | |
| US3135788A (en) * | 1959-09-28 | 1964-06-02 | Nihon Zoki Seiyaku Kabushikika | Preparation of dl-carnitine hydrochloride from trimethylamine hydrochloride and epihalogenohydrin |
| US3462485A (en) * | 1965-03-12 | 1969-08-19 | Belge Produits Chimiques Sa | Process for the preparation of l- and d-carnitine chlorides |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3344085A1 (de) * | 1982-12-06 | 1984-06-07 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A., Rom/Roma | Verfahren zur herstellung von l-carnitin und zwischenprodukte fuer das verfahren |
| US4788322A (en) * | 1987-07-31 | 1988-11-29 | Merck & Co., Inc. | Process for preparing ACHPA |
| US4895979A (en) * | 1988-02-19 | 1990-01-23 | Takasago International Corporation | Process for preparing carnitine |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2518813A1 (de) | 1975-11-06 |
| AR207361A1 (es) | 1976-09-30 |
| ZA752563B (en) | 1976-03-31 |
| IE41115L (en) | 1975-10-26 |
| DE2518813C2 (de) | 1983-09-15 |
| FR2268787B1 (ru) | 1980-05-09 |
| IT1035450B (it) | 1979-10-20 |
| AT342792B (de) | 1978-04-25 |
| NO751472L (ru) | 1975-10-28 |
| RO66137A (ro) | 1980-02-15 |
| CH589604A5 (ru) | 1977-07-15 |
| CA1034143A (en) | 1978-07-04 |
| ATA320575A (de) | 1977-08-15 |
| BE828456A (fr) | 1975-10-27 |
| BG26371A3 (bg) | 1979-03-15 |
| NL7504852A (nl) | 1975-10-28 |
| SE7504782L (sv) | 1975-10-27 |
| LU72363A1 (ru) | 1977-02-03 |
| SU544366A3 (ru) | 1977-01-25 |
| FR2268787A1 (ru) | 1975-11-21 |
| GB1448081A (en) | 1976-09-02 |
| IE41115B1 (en) | 1979-10-24 |
| DD119575A5 (ru) | 1976-05-05 |
| AU8042675A (en) | 1976-10-28 |
| IN144611B (ru) | 1978-05-20 |
| BR7502510A (pt) | 1976-03-03 |
| SE404691B (sv) | 1978-10-23 |
| JPS50148312A (ru) | 1975-11-27 |
| DK174575A (da) | 1975-10-27 |
| ES436902A1 (es) | 1977-01-01 |
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